58-85-5 Usage
Physicochemical property
Biotin is widely distributed in animals and plants, and the natural presence of biotin is mainly in the form of binding with other molecules. The biochemical structure of biotin includes a shuttle chain containing five carbon atoms and two five-membered heterocycles. In vivo the shuttle of the side chain binds with lysine s residue of enzyme protein, playing a role of coenzyme. Biotin may have 8 different isomers, of which only D-biotin has biological activity. Under normal circumstances, biotin is quite stable, only in the strong acid, alkali, formaldehyde and UV treatment will be destroyed. Biotin is the carrier of carboxyl in the carboxylation reaction required large ATP. The carboxyl group is temporarily bound to a nitrogen atom on the bicyclic ring system of biotin, such as in the reaction of pyruvate carboxylase catalyzing the pyruvate carboxylation of oxaloacetate.
Figure1: The structural formula of the biotin molecule
Physiological function
Biotin is necessary for cell growth, the production of fatty acids, and the metabolism of fats and amino acids. It plays a role in the citric acid cycle, which is the process by which biochemical energy is generated during aerobic respiration. Biotin is a coenzyme for carboxylase enzymes, involved in the synthesis of fatty acids, isoleucine, and valine, and in gluconeogenesis. In addition, biotin is widely used throughout the biotechnology industry to conjugate proteins for biochemical assays.
We need biotin about 100 to 300 micrograms per day. There is an antibiotic protein that could combine with biotin in the egg white egg. After combining, it cannot be absorbed by the digestive tract; resulting in animal biotin deficiency, at the same time loss of appetite, glossitis, dermatitis dermatitis, hair removal and so on. However, there is no case of biotin deficiency on human, probably because in addition to food sources, intestinal bacteria can also synthesize biotin. Biotin is a coenzyme of a lot of enzymes in the human body. It participates in the metabolism of aliphatic acid, carbohydrate, vitamin B12, folic acid and pantothenic acid; promoting synthesis of protein and urea, and also promoting excretion.
Help fat, glycogen and amino acids for normal synthesis and metabolism in the human body;
Promote the normal operation and growth of sweat glands, nerve tissue, bone marrow, male gonads, skin and hair, and reduce eczema, dermatitis symptoms;
Prevent white hair and hair loss, contribute to the treatment of baldness;
Relieve muscle pain;
Promote synthesis and excretion of urea, purine synthesis and oleic acid biosynthesis;
For the treatment of atherosclerosis, stroke, dyslipidemia, hypertension, coronary heart disease and blood circulation disorders.
Biotin and fat metabolism
As a coenzyme of phthalocyanine coenzyme A, Biotin is involved in the synthesis of fatty acids, catalyzing the formation of glycine CoA. The reaction is the first step in the synthesis of fatty acids, and then through the cytoplasmic multi-enzyme complex and fatty acid synthase synthesize palmitic acid from the phthalocyanine-CoA. In the prolongation of carbon chain in the fatty acid, the propanedio phthalide-ACP is involved in the reaction as a donor of the dicarbon unit, and the dipropyl phthalide-ACP is derived from the phthalide-CoA. It can be seen that biotin is necessary for the synthesis of fatty acids and the extension of carbon chains in fatty acid. Biotin deficiency can lead to abnormal lipid metabolism, resulting in changes of fatty acid composition in the body. In addition, synthesis of saturated fatty acid decreased, synthesis of triglyeeride increased, and fat in the liver and kidney increased by 2 to 5 times. Biotin-deficient diets increase the rate of desiccation of palmitic acid in liver tissue by five folds. Palmitic acid increased, at the same time stearic acid reduced. Biotin is also a necessary material for synthesis of long-chain unsaturated fatty acid and fatty acid metabolism. Biotin is also associated with the synthesis of acetylcholine and the metabolism of cholesterol. The lack of biotin reduces the ability of animals to synthesize arachidonic acid from linoleic acid, leading to the accumulation of linoleic acid in the body.
Biotin deficiency
Biotin deficiency appears to be rare, but some groups may be more susceptible.Biotin supplements are widely available but rarely necessary.
A deficiency can lead to:
Hair loss
A scaly red rash around the eyes, nose, mouth, and genitals
Cracks in the corner of the mouth
Sore tongue that may be magenta in color
Dry eyes
Loss of appetite
Other symptoms may include:
Depression
Lethargy and fatigue
Hallucinations
Insomnia
Numbness and tingling in the hands and feet
Impaired immune function and increased susceptibility to infections
Pregnant women appear to break down biotin more quickly, and this may lead to a marginal deficiency. Symptoms have not been observed, but such a deficiency could lead to developmental problems for the fetus.
Food source
Liver
Peanuts
Yeast
Whole-wheat bread
Cheddar cheese
Pork
Salmon
Sardines
Avocado
Raspberries
Bananas
Mushrooms
Cauliflower
Egg yolk
Egg white reduces the effectiveness of biotin from egg yolk in the body because it binds biotin and prevents it from being absorbed. People who consume only egg white for many years without biotin supplementation have a slight risk of not getting enough vitamin B7.
Processing food reduces levels of nutrients such as biotin, so raw cauliflower, for example, would provide more biotin than cooked cauliflower. A study published in Advances in Nutrition estimates biotic intake in North America and Western Europe at between 35 to 70 μg per day, or 143 to 287 mmol per day.
According to Oregon State University, biotin is not known to cause toxic effects. People with hereditary disorders of biotin metabolism tolerate doses of up to 200,000 mcg per day without any problems. Individuals with no biotin metabolism disorder who took doses of 5,000 mcg per day for 24 months had no adverse effects.
However, it is important to speak to a physician or dietitian before making any change to nutritional intake or using supplements.
Toxicity
Toxicity of biotin seems to be low. Treatment of seborrheic dermatitis with high doses of biotin did not detect abnormal protein metabolism or genetic errors and other metabolic abnormalities. Animal experiments also show that biotin toxicity is low.
Side effect
Bursts of cystic acne of jaw and chin are the most common side effects of biotin. The specific reason is not very clear. And usually this symptom will disappear by itself after a few weeks. There are also some nutritional supplements who report that acne symptoms can be reduced when the dose is limited to 2500 micrograms or less. In short, the situation experienced by each person is slightly different.
Life-threatening biotin is extremely rare. Eosinophilic pleural effusion is the only documented deadly case that causes a woman to die. She ingested a lot of biotin, along with vitamin B5. So far, it is unclear whether her death is caused by biotin, B5, or a mixture of both.
Healthy adults are less likely to develop biotin deficiency. This disease is common in excessive consumption of avidin (which can be found in raw eggs), or people with skin or hair disorders (such as phenylketonuria). The symptoms of lacking biotin usually take several years to show.
The study found that about 50% of pregnant women had a biotin deficiency problem. They lack a kind of enzyme to tell the body how to use biotin properly, which leads to a decline in metabolic function. Most physicians do not recommend biotin nutrition as a treatment because the trial for rats found that it had a risk of miscarriage and fetal defects.
Biotin is often recommended as nourishment for the promotion of hair and nail health. Because of the impact on carbohydrates, it is also often used to control body weight. Biotin supplements are known for their beauty and metabolic effects. The recommended dose ranges from 3 micrograms to 5000 micrograms per day, depending on the specific use. The side effects are relatively rare, and it is relatively easy to control even if the side effects appear, so it is a safe nutritional supplements.
Distinguishing test
The warm water saturated solution of the sample could cause the drop of the bromine test solution (TS-46) to fade.
Content analysis
Accurately weighed the sample about 500mg, mixed with 100ml of water, plus phenolphthalein test solution (TS-167) a few drops, with 0.1mol/L sodium hydroxide solution slowly added to the suspension in continuous heating and stirring, until we got pink suspension. 0.1 mol/L sodium hydroxide per ml is equivalent to 24.43 mg biotin (C10Hl6N2O3S).
Applications
As a feed additive, it is mainly used for poultry and sow feed. Usually the premixed mass fraction is 1%-2%.
It is nutritional supplement. According to China GB2760-90 regulations, it could be used as a food industry as a processing aid. It has physiological functions to prevent skin diseases and promote lipid metabolism and so on.
It is carboxylase coenzyme, involved in many carboxylation reactions, and is an important coenzyme in the metabolism of sugar, protein and fat.
It is used as food fortifier. It is used for infant food with amount of 0.1~0.4mg/kg, in the drinking liquid 0.02~0.08mg/kg.
It could be used for labeling proteins, antigens, antibodies, nucleic acids (DNA, RNA) and so on.
References
https://www.ulprospector.com/en/na/PersonalCare/Detail/473/317131/D-Biotin
https://en.wikipedia.org/wiki/Biotin
http://www.medicalnewstoday.com/articles/219718.php
http://www.selleckchem.com/products/biotin-vitamin-b7.html
Chemical Properties
White powder
Originator
Biotin,Solgar
Uses
Different sources of media describe the Uses of 58-85-5 differently. You can refer to the following data:
1. vasodilator
2. vitamin B complex
Definition
ChEBI: An organic heterobicyclic compound that consists of 2-oxohexahydro-1H-thieno[3,4-d]imidazole having a valeric acid substituent attached to the tetrahydrothiophene ring. The parent of the class of biotins.
Manufacturing Process
4-Carbomethoxy-2-(4,5-dihydrothiophen-3(2H)-one)valeric acid methyl ester
was prepared from 4,5-dihydrothiophene as it was described in Baker et al., J.
Org. Chem., 12, 167 (1947).
A solution of 60.0 g (0.182 mole) this ester in 550 ml absolute ethanol was
treated with 91.6 g (1.45 moles) of ammonium formate. The reaction mixture
refluxed for 5.0 hours. Then it was cooled, concentrated, and partitionated in
a separatory funnel between 200 ml dichloromethane and 150 ml water. The
aqueous phase was extracted three times with 50 ml portions of
dichloromethane. The organic extracts were collected, dried over anhydrous
sodium sulfate, and evaporated. 50 g (0.182 mole, 100%) 3-amino-4-
carbomethoxy-2,5-dihydro-2-thiophenevaleric acid methyl ester was obtained
as a colorless oil.
To a solution of 27.3 g (1 mole) of 3-amino-4-carbomethoxy-2,5-dihydro-2-
thiophenevaleric acid methyl ester in 250 ml dry methanol was added 4.0 g
(0.1 mole) of sodium hydroxide pellets. The reaction mixture was refluxed 4.0
hrs, cooled and concentrated to a volume of 50 ml. The residue was taken up
in 80 ml dichloromethane and transfered to a separatory funnel. After the
addition of 150 ml of 10% by weight aqueous sodium bicarbonate solution,
the aqueous layer was extracted twice with 50 ml portions of
dichloromethane. The organic phases were combined, dried over anhydrous
sodium sulfate, and evaporated to yield 6.4 g (0.0234 mole) of recovered
starting material. The aqueous phase was adjusted to pH 1 with 6 N
hydrochloric acid and extracted three times with 75 ml portions of
dichloromethane. The organic phases were pooled, dried over anhydrous
sodium sulfate, and evaporated to yield 18.3 g (0.071 mole, 71%) of 3-
amino-4-carbomethoxy-2,5-dihydro-2-thiophenevaleric acid as a tan solid,
upon trituration with pet. ether.
The recovered starting material, 6.4 g (0.0234 mole) was dissolved in 70 ml
dry methanol and treated with 1.0 g (0.025 mole) sodium hydroxide. The
mixture was refluxed 5.0 hrs, cooled concentrated, and taken up in 80 ml
dichloromethane. The organic phase was treated in a separatory funnel with
100 ml of 10% by weight aqueous sodium bicarbonate solution. The aqueous
phase was extracted twice with 40 ml portions of dichloromethane. The
aqueous phase was acidified to pH 1 with 6 N hydrochloric acid and extracted
two times with 50 ml portions of dichloromethane. The organic phases were
cooled, dried over anhydrous sodium sulfate, and evaporated to dryness to
afford an additional 5.3 g (0.021 mole, 21%) of 3-amino-4-carbomethoxy-
2,5-dihydro-2-thiophenevaleric acid; m.p. 98°-102°C.
Therapeutic Function
Vitamin
General Description
Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.Biotin is a water-soluble vitamin, essential for amino acids and carbohydrates metabolism. It is involved in de novo synthesis of purine nucleotides and plays a role in gene expression and DNA replication.
Biochem/physiol Actions
Biotin is a vital cofactor for carboxylase enzymes in several metabolic?pathways. It also functions as a coenzyme in the metabolism of fatty acids, isoleucine and valine. Biotin assists the transfer of carbon dioxide and also sustains a steady blood sugar level. Biotin is implicated in gluconeogenesis and citric acid cycle. It?is involved in?keratin?synthesis and hence?is used as?a supplement?for skin, hair and nail growth. Biotin is required for cell growth, production of fatty acids and the metabolism of fats and amino acids.
Safety Profile
An experimental
teratogen. Experimental reproductive
effects. When heated to decomposition it
emits toxic fumes of NOx and SOx.
Purification Methods
D-(+)-Biotin crystallises from hot water in fine long needles with a solubility of 22 mg/100mL at 25o. Its solubility in 95% EtOH is 80 mg/100 mL at 25o. Its isoelectric point is at pH 3.5. Store solid and solutions under sterile conditions because it is susceptible to mould growth. [Confalone J Am Chem Soc 97 5936 1975, Wolf et al. J Am Chem Soc 67 2100 1945, Synthesis: Ohuri & Emoto Tetrahedron Lett 2765 1975, Harris et al. J Am Chem Soc 66 1756 1944.] The (+)-methyl ester has m 166-167o (from MeOH/Et2O), [] D 22 +57o (c 1, CHCl3) [du Vigneaud et al. J Biol Chem 140 643, 763 1941]; the (+)-S-oxide has m 200-203o, [] D 20 +130o (c 1.2, 0.1N NaOH) [Melville J Biol Chem 208 495 1954]; the SS-dioxide has m 274-275o(dec, 268-270o), and the SS-dioxide methyl ester has m 239-241o (from MeOH/Et2O) [Hofmann et al. J Biol Chem 141 207, 213 1941]. [Beilstein 27 III/IV 7979.]
Check Digit Verification of cas no
The CAS Registry Mumber 58-85-5 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 8 respectively; the second part has 2 digits, 8 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 58-85:
(4*5)+(3*8)+(2*8)+(1*5)=65
65 % 10 = 5
So 58-85-5 is a valid CAS Registry Number.
InChI:InChI=1/C10H16N2O3S/c13-8(14)4-2-1-3-7-9-6(5-16-7)11-10(15)12-9/h6-7,9H,1-5H2,(H,13,14)(H2,11,12,15)/p-1/t6-,7-,9+/m0/s1
58-85-5Relevant articles and documents
SYSTEMS AND METHODS FOR DETECTION OF TARGET ANALYTES USING SELECTIVELY CLEAVABLE BONDS
-
, (2021/09/10)
The invention described herein is directed to methods of isolation and detection of target analytes in a sample. The target analytes are coupled to analyte detection particles which comprise base particles having labels and affinity agents coupled thereto by linker arms. The linker arms form bonds with the labels and target analytes and are cleavable under different label and affinity cleavable conditions. Systems and methods for preparing and using the analyte detection particles are also disclosed.
Solution Dynamics of Hybrid Anderson-Evans Polyoxometalates
Salazar Marcano, David E.,Lentink, Sarah,Moussawi, Mhamad A.,Parac-Vogt, Tatjana N.
supporting information, p. 10215 - 10226 (2021/05/31)
Understanding the stability and speciation of metal-oxo clusters in solution is essential for many of their applications in different areas. In particular, hybrid organic-inorganic polyoxometalates (HPOMs) have been attracting increasing attention as they combine the complementary properties of organic ligands and metal-oxygen nanoclusters. Nevertheless, the speciation and solution behavior of HPOMs have been scarcely investigated. Hence, in this work, a series of HPOMs based on the archetypical Anderson-Evans structure, δ-[MnMo6O18{(OCH2)3C-R}2]3-, with different functional groups (R = -NH2, -CH3, -NHCOCH2Cl, -NCH(2-C5H4N) {pyridine; -Pyr}, and -NHCOC9H15N2OS {biotin; -Biot}) and countercations (tetrabutylammonium {TBA}, Li, Na, and K) were synthesized, and their solution behavior was studied in detail. In aqueous solutions, decomposition of HPOMs into the free organic ligand, [MoO4]2-, and free Mn3+ was observed over time and was shown to be highly dependent on the pH, temperature, and nature of the ligand functional group but largely independent of ionic strength or the nature of the countercation. Furthermore, hydrolysis of the amide and imine bonds often present in postfunctionalized HPOMs was also observed. Hence, HPOMs were shown to exhibit highly dynamic behavior in solution, which needs to be carefully considered when designing HPOMs, particularly for biological applications.
METHOD FOR PRODUCING BIOTIN
-
Paragraph 0067-0083, (2021/02/25)
To provide a production method for obtaining high-purity biotin at good yields.SOLUTION: A method for producing biotin includes a process in which a composition comprising biotin represented by the formula (I) is brought into contact with hydrosulfite salt, before the biotin is extracted.SELECTED DRAWING: None
Selective modification of sulfamidate-containing peptides
Busto, Jesús H.,Jiménez-Osés, Gonzalo,Mazo, Nuria,Navo, Claudio D.,Peregrina, Jesús M.
supporting information, p. 6265 - 6275 (2020/09/07)
Hybrid peptides whose N-terminal residues are activated in the form of α-methylisoserine-derived cyclic sulfamidates exhibit rich reactivity as electrophiles, allowing site- and stereoselective modifications at different backbone and side chain positions.
Selective Modification of Ribosomally Synthesized and Post-Translationally Modified Peptides (RiPPs) through Diels–Alder Cycloadditions on Dehydroalanine Residues
de Vries, Reinder H.,Viel, Jakob H.,Oudshoorn, Ruben,Kuipers, Oscar P.,Roelfes, Gerard
supporting information, p. 12698 - 12702 (2019/09/12)
We report the late-stage chemical modification of ribosomally synthesized and post-translationally modified peptides (RIPPs) by Diels–Alder cycloadditions to naturally occurring dehydroalanines. The tail region of the thiopeptide thiostrepton could be modified selectively and efficiently under microwave heating and transition-metal-free conditions. The Diels–Alder adducts were isolated and the different site- and endo/exo isomers were identified by 1D/2D 1H NMR. Via efficient modification of the thiopeptide nosiheptide and the lanthipeptide nisin Z the generality of the method was established. Minimum inhibitory concentration (MIC) assays of the purified thiostrepton Diels–Alder products against thiostrepton-susceptible strains displayed high activities comparable to that of native thiostrepton. These Diels–Alder products were also subjected successfully to inverse-electron-demand Diels–Alder reactions with a variety of functionalized tetrazines, demonstrating the utility of this method for labeling of RiPPs.
Method for Producing Intermediate of Biotin and Method for Producing Biotin
-
, (2020/01/08)
In the method, a trione compound represented by the following formula (1) is (i) reduced by NaAlH2(OCH2CH2OCH3)2 and subsequently further reduced by a metal borohydride salt, or (ii) reduced by calcium borohydride, thereby producing an amide alcohol compound represented by the following formula (3) (wherein, R1 and R2 may be the same or different and each represents a hydrogen atom or a protecting group of an ureylene group; R4 represents an alkyl group, an aralkyl group, or an aryl group; and each of R5, R6, and R7 represents a hydrogen atom, an alkyl group, an alkoxy group, or a halogen atom).
A preparation method of d - biotin (by machine translation)
-
Paragraph 0037; 0038; 0039; 0040; 0041; 0042; 0043-0060, (2019/05/04)
The invention belongs to the field of organic synthesis, in particular relates to a preparation method of d - biotin, the method comprises the following steps: the double-benzyl biotin with three boron halide and organic solution, in the absence of the organic solvent in the water environment, under the protection of inert gas, through the one-step reaction to remove the double-benzyl, get d - biotin. The present invention provides a simple and convenient, safe, high yield, high purity of methylsulphonyl preparation method of d - biotin, is suitable for industrial production. (by machine translation)
A dibenzyl biotin by d - biotin method of preparation
-
Paragraph 0033-0038, (2019/02/26)
The invention discloses a method for preparing d-biotin from dibenzyl biotin. The method comprises the following steps: 1, adding an inorganic acid and zinc powder to an aqueous solution of dibenzyl biotin; and 2, reacting at 40-70DEG C, and post-processing after the raction ends to obtain d-biotin. The d-biotin is prepared through removing benzyl groups by using the zinc powder/inorganic acid system under mild conditions, so the method has the advantages of simple operation and easy industrialization; and the purity of the obtained d-biotin is greater than 99.5%, and the mole yield of the obtained d-biotin is greater than 90%, so compared with the prior art, the method has substantial progress.
Synthesis method of d-biotin
-
Paragraph 0109-0118, (2019/04/04)
The invention discloses a synthesis method of d-biotin. The synthesis method comprises the following steps: taking cysteine hydrochloride, benzaldehyde and benzyl isocyanate as starting materials, andsubjecting the starting materials to condensation, cyclization, reduction, condensation, oxidation, reduction, cyclization, elimination, catalytic hydrogenation and debenzylation sequentially to obtain the d-biotin. The method has the advantages that the raw materials are cheap and easy to obtain, the safety is good, the reaction conditions are mild and easy to control, the production cost is lowered, green and environmental protection is achieved, the reaction yield is high, separation is easy, and the purity of the obtained d-biotin is high.
Method for catalytic synthesis of biotin by using high-recycling-activity palladium-carbon catalyst
-
Paragraph 0019; 0020-0057, (2019/04/10)
The invention discloses a method for catalytic synthesis of biotin by using a high-recycling-activity palladium-carbon catalyst. The method comprises the following steps: palladium-carbon is taken asa catalyst to catalyze synthesis of biotin by hydrogenation of a biotin intermediate cis-2-oxo-1,3-dibenzyl-4-(4-carboxybutyl-1-ene)hexahydro-1H-thieno[3,4-d]imidazole, wherein activated carbon is taken as a carrier of the catalyst, the carrier is activated by hydrogen peroxide after being subjected to high-temperature treatment in an ammonia atmosphere, and then the pretreated activated carbon isobtained; the soluble palladium compound is dissolved in water, a nitrogen-containing compound is added, and reflux stirring is carried out to obtain a palladium precursor solution; and the pretreated activated carbon is pulped by using alcohol water, then a palladium precursor solution is added, an alkali is added for controlling the pH value of the system to be 6-12, and then reduction is carried out by a reducing agent to obtain the palladium-carbon catalyst. Compared with the prior art, the method disclosed by the invention has the advantages that activity of the catalyst is high, performance of the catalyst is stable, the number of recycling times in biotin synthesis can be greatly increased, and production cost can be reduced.
